𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Bossi (2026)

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Our top choices for Bossi hotels

A courtyard with stone walls, arched windows, and potted plants.

A rustic interior with a stone wall, a wooden staircase, and a view of the outdoors.

A swimming pool with a clear view of the surrounding landscape, including trees and distant hills.

An outdoor courtyard with stone walls, arched windows, and potted plants.

1. Castello di Bossi

Castelnuovo Berardenga

CESAR JAVIER

S$221

includes taxes & fees

20 Oct - 21 Oct

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An interior corridor with arches, columns, and a brick wall.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

2. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

S$148

includes taxes & fees

20 Oct - 21 Oct

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

3. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

S$226

includes taxes & fees

25 Oct - 26 Oct

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

4. Agriturismo San Sano

Gaiole in Chianti

Glen

S$108

includes taxes & fees

18 Oct - 19 Oct

A modern building with a sign reading "Palace Hotel."

A red building with a reception sign, a bicycle, potted plants, and luggage.

A buffet setup with various food items including yogurt cups, fruits, and a bowl of grapes.

5. Palace Hotel Due Ponti

Due Ponti

Adam

S$113

includes taxes & fees

1 Nov - 2 Nov

A terrace with multiple sun loungers and a scenic view of green fields and hills.

A modern hotel room with a bed, a small table with a hat, a red chair, a window with curtains, and a bathroom with a glass shower enclosure.

An indoor swimming pool with lounge chairs and a view of the countryside.

A spacious living area with a wooden coffee table, a large potted plant, and a sofa.

6. Precise House Montaperti Siena

Asciano

Dieter

S$125

includes taxes & fees

1 Nov - 2 Nov

A table set for dining with a scenic view of rolling hills and distant mountains.

A courtyard with brick buildings, a column, and potted plants.

A spacious dining area with round tables and wicker chairs, a patterned rug, and a wooden ceiling.

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

7. Castello di Leonina Relais

Asciano

Meghan

S$167

includes taxes & fees

23 Oct - 24 Oct

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A room with a view of a forest through a window, a table with a lamp, and a chair.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

8. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

S$396

includes taxes & fees

4 Nov - 5 Nov

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

9. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

S$143

includes taxes & fees

22 Oct - 23 Oct

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

A hotel entrance with a sign reading "HOTEL EXPO".

An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.

A modern living room with a glass coffee table, white sofas, and decorative plants.

10. Hotel Executive

Scacciapensieri

Susan

S$132

includes taxes & fees

1 Nov - 2 Nov

A pathway lined with trees and a large pot in the center.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

A breakfast buffet with pastries and a coffee machine.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

11. Villa Montarioso

Montarioso

Michael

S$122

includes taxes & fees

3 Nov - 4 Nov

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A building with arched windows, a courtyard with a pond, and a metal fence.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

12. Hotel Casafrassi

Castellina in Chianti

Stuart

S$94

includes taxes & fees

6 Oct - 7 Oct

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

13. Four Points by Sheraton Siena

Scacciapensieri

Ralph

S$200

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

A bathroom with a sink, mirror, and shower.

A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.

14. Sangallo Park Hotel

Vico Alto

Linda

S$129

includes taxes & fees

2 Nov - 3 Nov

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

15. The Club House

Castelnuovo Berardenga

Natalyn

S$504

includes taxes & fees

1 Nov - 2 Nov

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A large, historic building with a covered patio and a well-maintained garden.

A room with a large window offering a view of a landscaped garden with trees and a pathway.

A swimming pool surrounded by lush greenery and a stone pathway.

16. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

S$248

includes taxes & fees

21 Oct - 22 Oct

A table set for breakfast with a scenic view of hills and a cloudy sky.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

17. Palazzo di Valli

Siena

Payton

S$173

includes taxes & fees

3 Nov - 4 Nov

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A table set for breakfast with various dishes, drinks, and a newspaper.

18. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

S$696

includes taxes & fees

21 Oct - 22 Oct

A building with a sign reading 'HOTEL SAN CARLO.' It features a flat roof, a large entrance with glass doors, and a paved courtyard.

A conference room with a long table, blue chairs, a whiteboard, and a projector screen.

A bakery display with various pastries and bread, including croissants and cakes, with labels indicating the type of pastry.

19. Best Western Hotel San Marco

Siena

C.K.

S$134

includes taxes & fees

1 Nov - 2 Nov

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A rustic stone building with a garden in front.

A person relaxing in a hot tub with a view of a building and trees in the background.

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

20. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

S$181

includes taxes & fees

15 Oct - 16 Oct

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Top Bossi Hotel Reviews

Borgo Scopeto Wine & Country Relais

8/10 Good

"Concierge desk - Francesca - was off the charts! Was hoping for more modernized room with better views"

Palazzo Ravizza

10/10 Excellent

"We spent four nights in Siena as a base for other tuscan adventures. Loved the authenticity of the piazza. The staff are exceptional and very attentive. The contential breakfast is well appointed and available coffee choices excellent. Don't miss sunset in the back garden bellicimo."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Fattoria di Vegi

10/10 Excellent

"The entire estate was perfectly curated, every aspect was completely flawless. Food and wine…. 10/10. Best place we’ve ever stayed."

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Il Chiostro del Carmine

10/10 Excellent

"Room clean large spacious staff friendly helpful good quiet location great views"

Hotel Borgo San Luigi

8/10 Good

"Great breakfast and clean room. However, not a very kid friendly with no high chair available in the room and the few ones in the restaurant were broken or dirty. Good place for adulte."

Hotel Minerva

10/10 Excellent

"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."

More cheap stays in Bossi

Cannon d'Oro

Via Montanini 28 Siena SI

S$80

5 Nov - 6 Nov

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

S$117

5 Nov - 6 Nov

includes taxes & fees

7.8/10 Good! (447 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

S$124

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

S$134

5 Nov - 6 Nov

includes taxes & fees

8.8/10 Excellent! (109 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

S$221

20 Oct - 21 Oct

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Frequently asked questions

Where is the best place to stay in Bossi?

Hotel Athena, located 7.4 mi (12 km) from the heart of Bossi, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are La Certosa di Pontignano and Grand Hotel Continental Siena – Starhotels Collezione. See all available top hotels, or vacation rentals in Bossi.

What are some of the best holiday rentals that Bossi has to offer?

Borgo Argiano: This holiday home rental outside of Bossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Bossi.

If I need to cancel my hotel reservation in Bossi, will I receive a refund?

Yes! Most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Bossi.

What's the best dog-friendly accommodation option in Bossi?

Castello di Bossi is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Bossi.

What are some accommodation options with pools in Bossi?

Fattoria di Vegi: Offers a rooftop terrace, an outdoor pool and a snack bar/deli. Another choice that features an on-site pool is Castello di Spaltenna- Small Luxury Hotels of the World. View all hotels with pools in Bossi.

What is staying in Bossi like?

Travellers to Bossi will find plenty to explore and enjoy. In Bossi, there are 20 hotels and other accommodation options to choose from. Find out more about Bossi.

What are the top places to visit in Bossi?

Places to visit in the wider area include Castle of Brolio, Siena Circuit and Cantalici Winery. You'll also find Meleto Castle and Villa a Sesta Polo Club in the area. Take a look at what more there is to see and do in Expedia's Bossi guide.

What's the seasonal weather like in Bossi?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Bossi is 946 mm.

Bossi Hotels from S$69

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Bossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Bossi hotels

1. Castello di Bossi

2. La Certosa di Pontignano

3. Castello di Tornano Wine Resort

4. Agriturismo San Sano

5. Palace Hotel Due Ponti

6. Precise House Montaperti Siena

7. Castello di Leonina Relais

8. Dievole Wine Resort

9. Ultimo Mulino Wellness Country Hotel

10. Hotel Executive

11. Villa Montarioso

12. Hotel Casafrassi

13. Four Points by Sheraton Siena

14. Sangallo Park Hotel

15. The Club House

16. Villa Scacciapensieri Boutique Hotel

17. Palazzo di Valli

18. Hotel Le Fontanelle

19. Best Western Hotel San Marco

20. Belvedere di San Leonino

Top Bossi Hotel Reviews

Borgo Scopeto Wine & Country Relais

Palazzo Ravizza

Four Points by Sheraton Siena

Fattoria di Vegi

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Il Chiostro del Carmine

Hotel Borgo San Luigi

Hotel Minerva

More cheap stays in Bossi

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Albergo Centrale

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

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